It is OK to get things wrong, too. I mean, ideally, you'll look for romantic partners outside the workplace, but if you must look at work, it can still be OK. I

It is OK to get things wrong, too. I mean, ideally, you'll look for romantic partners outside the workplace, but if you must look at work, it can still be OK. If you flirt, you think the other person is flirting back, you ask them out, and they reject you, that is neither sexual harassment nor a grave offense. Example approach (in our scenario, this is toward the end of a workday, which is when you would want to do anything like this): "Hey, I've been having a lot of fun working with you, would you want to get dinner together sometime?" "Oh, I'm sorry, I'm [not looking for a relationship right now|seeing someone else|not interested in you that way|...]." "Oh, shoot. Well, I'll see you tomorrow then." (Go home.) It may be a little awkward, but if you do things respectfully, then it will probably not ruin the working relationship. And more importantly, you'll have flattered the person you're working with, not creeped them out or made their workplace environment hostile, not cemented yourself in their mind as a total asshole, and not put yourself at risk for getting fired for harassment. Of course, you will never do this to one of your reports or their transitive reports unless you would like to lose your job. Only peers or members of another org.